Forming Bonds While Breaking Old Ones: Isomer-Dependent Formation of H 3 O + from Aminobenzoic Acid During X-ray-Induced Fragmentation

Abid, Abdul Rahman; Veteläinen, Onni; Boudjemia, Nacer; Pelimanni, Eetu; Kivimäki, Antti; Alatalo, Matti; Huttula, Marko; Björneholm, Olle; Patanen, Minna

doi:10.1021/acs.jpca.2c06869

Title: Forming Bonds While Breaking Old Ones: Isomer-Dependent Formation of H ₃ O ⁺ from Aminobenzoic Acid During X-ray-Induced Fragmentation

Journal Article · Tue Feb 07 00:00:00 EST 2023 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory

DOI:https://doi.org/10.1021/acs.jpca.2c06869· OSTI ID:1923723

Abid, Abdul Rahman ^[1]; Veteläinen, Onni ^[2]; Boudjemia, Nacer ^[2];

^[2];

^[3]; Alatalo, Matti ^[2]; Huttula, Marko ^[2];

^[4];

^[2]

Nano and Molecular Systems Research Unit, University of Oulu, 90570 Oulu, Finland, Molecular and Condensed Matter Physics, Uppsala University, 75120 Uppsala, Sweden
Nano and Molecular Systems Research Unit, University of Oulu, 90570 Oulu, Finland
Nano and Molecular Systems Research Unit, University of Oulu, 90570 Oulu, Finland, MAX IV Laboratory, Lund University, 22100 Lund, Sweden
Molecular and Condensed Matter Physics, Uppsala University, 75120 Uppsala, Sweden

Intramolecular hydrogen transfer, a reaction where donor and acceptor sites of a hydrogen atom are part of the same molecule, is a ubiquitous reaction in biochemistry and organic synthesis. In this work, we report hydronium ion (H₃O⁺) production from aminobenzoic acid (ABA) after core-level ionization with soft X-ray synchrotron radiation. The formation of H₃O⁺ during the fragmentation requires that at least two hydrogen atoms migrate to one of the oxygen atoms within the molecule. The comparison of two structural isomers, ortho- and meta-ABA, revealed that the production of H₃O⁺ depends strongly on the structure of the molecule, the ortho-isomer being much more prone to produce H₃O⁺. The isomer-dependency suggests that the amine group acts as a donor in the hydrogen transfer process. In the case of ortho-ABA, detailed H₃O⁺ production pathways were investigated using photoelectron-photoion-photoion coincidence (PEPIPICO) spectroscopy. It was found that H₃O⁺ can result from a direct two-body dissociation but also from sequential fragmentation processes.

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Research Organization:: Univ. of Chicago, IL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division; Swedish Research Council (SRC); Swedish Governmental Agency for Innovation Systems; Formas; Marie Skłodowska-Curie I4Future; EU Framework Programme for Research and Innovation Horizon 2020

Grant/Contract Number:: DEAC02-06CH11357; AC02-06CH11357; 2018-07152; 730872; 2018-04969; 2019-02496; 713606

OSTI ID:: 1923723

Alternate ID(s):: OSTI ID: 1957494

Journal Information:: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory, Journal Name: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory Vol. 127 Journal Issue: 6; ISSN 1089-5639

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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Title: Forming Bonds While Breaking Old Ones: Isomer-Dependent Formation of H ₃ O ⁺ from Aminobenzoic Acid During X-ray-Induced Fragmentation